2-Methoxyethoxymethyl chloride, 94%, Thermo Scientific Chemicals

General References:

1. JH Rigby.; JAZ Wilson. Removal of methoxyethoxymethyl ethers with trimethylsilyl chloride-sodium iodide. Tetrahedron letters. 198425(14) , 1429-1432.
2. RS Gross.; DS Watt. A Lewis acid-catalyzed procedure for the conversion of 2-methoxyethoxymethyl ethers to carboxylic esters. Synthetic Communications. 198717(15) , 1749-1760.
3. Reagent for the protection of OH groups, in the presence of a base, e.g. NaH in THF or N-Ethyl diisopropyl amine, A11801. The MEM-group is more readily and cleanly introduced than methoxymethyl (MOM) and is stable to a wide range of conditions. The MEM group is selectively cleaved by mild Lewis acids, e.g. ZnBr₂ or TiCl₄: Tetrahedron Lett., 809, 4701, 4705 (1976); 24, 3969 (1983), PPTS: Synth. Commun., 13, 1021 (1983), in situ generated TMS iodide: Tetrahedron Lett., 25, 1429 (1984), or CeCl₃: Org. Lett., 3, 1149 (2001).
4. For use in the protection of the OH groups in serine and threonine during peptide synthesis, see: Int. J. Pept. Prot. Res., 25, 544 (1985). See also Appendix 6.
5. MEM ethers have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereocontrolled addition of ɑ-methoxyvinyllithium to a carbonyl in the synthesis of taxusin: J. Am. Chem. Soc., 110, 6558 (1988), and subsequently in the addition of MeLi to an ɑß-unsaturated sulfone: J. Am. Chem. Soc., 113, 3085 (1991); see 2,2,2-Trifluoroethanol, A10788, for another example.
6. For cleavage by PPTS, see: Synth. Commun., 1021 (1983). For cleavage by TMS chloride/ NaI or, less effectively, by preformed TMS iodide, see: Tetrahedron Lett., 25, 1429 (1984).